Evaluation of a model photo-caged dehydropeptide as a stimuli-responsive supramolecular hydrogel

Detalhes bibliográficos
Autor(a) principal: Jervis, Peter John
Data de Publicação: 2021
Outros Autores: Hilliou, L., Pereira, Renato B., Pereira, David M., Martins, J. A. R., Ferreira, Paula M. T.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/72634
Resumo: Short peptides capped on the <i>N</i>-terminus with aromatic groups are often able to form supramolecular hydrogels, via self-assembly, in aqueous media. The rheological properties of these readily tunable hydrogels resemble those of the extracellular matrix (ECM) and therefore have potential for various biological applications, such as tissue engineering, biosensors, 3D bioprinting, drug delivery systems and wound dressings. We herein report a new photo-responsive supramolecular hydrogel based on a “caged” dehydropeptide (CNB-Phe-ΔPhe-OH <b>2</b>), containing a photo-cleavable carboxy-2-nitrobenzyl (CNB) group. We have characterized this hydrogel using a range of techniques. Irradiation with UV light cleaves the pendant aromatic capping group, to liberate the corresponding uncaged model dehydropeptide (H-Phe-ΔPhe-OH <b>3</b>), a process which was investigated by <sup>1</sup>H NMR and HPLC studies. Crucially, this cleavage of the capping group is accompanied by dissolution of the hydrogel (studied visually and by fluorescence spectroscopy), as the delicate balance of intramolecular interactions within the hydrogel structure is disrupted. Hydrogels which can be disassembled non-invasively with temporal and spatial control have great potential for specialized on-demand drug release systems, wound dressing materials and various topical treatments. Both <b>2</b> and <b>3</b> were found to be non-cytotoxic to the human keratinocyte cell line, HaCaT. The UV-responsive hydrogel system reported here is complementary to previously reported related UV-responsive systems, which are generally composed of peptides formed from canonical amino acids, which are susceptible to enzymatic proteolysis in vivo. This system is based on a dehydrodipeptide structure which is known to confer proteolytic resistance. We have investigated the ability of the photo-activated system to accelerate the release of the antibiotic, ciprofloxacin, as well as some other small model drug compounds. We have also conducted some initial studies towards skin-related applications. Moreover, this model system could potentially be adapted for on-demand “self-delivery”, through the uncaging of known biologically active dehydrodipeptides.
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spelling Evaluation of a model photo-caged dehydropeptide as a stimuli-responsive supramolecular hydrogelSupramolecularPeptideDehydropeptideHydrogelStimuli-responsivePhoto-responsiveCarboxy-2-nitrobenzylPhoto-labileRheologyDrug deliveryScience & TechnologyShort peptides capped on the <i>N</i>-terminus with aromatic groups are often able to form supramolecular hydrogels, via self-assembly, in aqueous media. The rheological properties of these readily tunable hydrogels resemble those of the extracellular matrix (ECM) and therefore have potential for various biological applications, such as tissue engineering, biosensors, 3D bioprinting, drug delivery systems and wound dressings. We herein report a new photo-responsive supramolecular hydrogel based on a “caged” dehydropeptide (CNB-Phe-ΔPhe-OH <b>2</b>), containing a photo-cleavable carboxy-2-nitrobenzyl (CNB) group. We have characterized this hydrogel using a range of techniques. Irradiation with UV light cleaves the pendant aromatic capping group, to liberate the corresponding uncaged model dehydropeptide (H-Phe-ΔPhe-OH <b>3</b>), a process which was investigated by <sup>1</sup>H NMR and HPLC studies. Crucially, this cleavage of the capping group is accompanied by dissolution of the hydrogel (studied visually and by fluorescence spectroscopy), as the delicate balance of intramolecular interactions within the hydrogel structure is disrupted. Hydrogels which can be disassembled non-invasively with temporal and spatial control have great potential for specialized on-demand drug release systems, wound dressing materials and various topical treatments. Both <b>2</b> and <b>3</b> were found to be non-cytotoxic to the human keratinocyte cell line, HaCaT. The UV-responsive hydrogel system reported here is complementary to previously reported related UV-responsive systems, which are generally composed of peptides formed from canonical amino acids, which are susceptible to enzymatic proteolysis in vivo. This system is based on a dehydrodipeptide structure which is known to confer proteolytic resistance. We have investigated the ability of the photo-activated system to accelerate the release of the antibiotic, ciprofloxacin, as well as some other small model drug compounds. We have also conducted some initial studies towards skin-related applications. Moreover, this model system could potentially be adapted for on-demand “self-delivery”, through the uncaging of known biologically active dehydrodipeptides.This work was supported by the Portuguese Foundation for Science and Technology (FCT) in the framework of the Strategic Funding of CQUM (UID/QUI/00686/2019) and of IPC (UID/CTM/50025/2019). L.H. acknowledges funding from the FCT Investigator Programme through grant IF/00606/2014. FCT, FEDER, PORTUGAL2020 and COMPETE2020 are also acknowledged for funding under research project PTDC/QUI-QOR/29015/2017 (POCI-01-0145-FEDER-029015).Multidisciplinary Digital Publishing Institute (MDPI)Universidade do MinhoJervis, Peter JohnHilliou, L.Pereira, Renato B.Pereira, David M.Martins, J. A. R.Ferreira, Paula M. T.2021-03-112021-03-11T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/72634engJervis, P.J.; Hilliou, L.; Pereira, R.B.; Pereira, D.M.; Martins, J.A.; Ferreira, P.M.T. Evaluation of a Model Photo-Caged Dehydropeptide as a Stimuli-Responsive Supramolecular Hydrogel. Nanomaterials 2021, 11, 704. https://doi.org/10.3390/nano110307042079-499110.3390/nano11030704https://www.mdpi.com/2079-4991/11/3/704info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T12:01:34Zoai:repositorium.sdum.uminho.pt:1822/72634Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T18:51:29.821184Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Evaluation of a model photo-caged dehydropeptide as a stimuli-responsive supramolecular hydrogel
title Evaluation of a model photo-caged dehydropeptide as a stimuli-responsive supramolecular hydrogel
spellingShingle Evaluation of a model photo-caged dehydropeptide as a stimuli-responsive supramolecular hydrogel
Jervis, Peter John
Supramolecular
Peptide
Dehydropeptide
Hydrogel
Stimuli-responsive
Photo-responsive
Carboxy-2-nitrobenzyl
Photo-labile
Rheology
Drug delivery
Science & Technology
title_short Evaluation of a model photo-caged dehydropeptide as a stimuli-responsive supramolecular hydrogel
title_full Evaluation of a model photo-caged dehydropeptide as a stimuli-responsive supramolecular hydrogel
title_fullStr Evaluation of a model photo-caged dehydropeptide as a stimuli-responsive supramolecular hydrogel
title_full_unstemmed Evaluation of a model photo-caged dehydropeptide as a stimuli-responsive supramolecular hydrogel
title_sort Evaluation of a model photo-caged dehydropeptide as a stimuli-responsive supramolecular hydrogel
author Jervis, Peter John
author_facet Jervis, Peter John
Hilliou, L.
Pereira, Renato B.
Pereira, David M.
Martins, J. A. R.
Ferreira, Paula M. T.
author_role author
author2 Hilliou, L.
Pereira, Renato B.
Pereira, David M.
Martins, J. A. R.
Ferreira, Paula M. T.
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Jervis, Peter John
Hilliou, L.
Pereira, Renato B.
Pereira, David M.
Martins, J. A. R.
Ferreira, Paula M. T.
dc.subject.por.fl_str_mv Supramolecular
Peptide
Dehydropeptide
Hydrogel
Stimuli-responsive
Photo-responsive
Carboxy-2-nitrobenzyl
Photo-labile
Rheology
Drug delivery
Science & Technology
topic Supramolecular
Peptide
Dehydropeptide
Hydrogel
Stimuli-responsive
Photo-responsive
Carboxy-2-nitrobenzyl
Photo-labile
Rheology
Drug delivery
Science & Technology
description Short peptides capped on the <i>N</i>-terminus with aromatic groups are often able to form supramolecular hydrogels, via self-assembly, in aqueous media. The rheological properties of these readily tunable hydrogels resemble those of the extracellular matrix (ECM) and therefore have potential for various biological applications, such as tissue engineering, biosensors, 3D bioprinting, drug delivery systems and wound dressings. We herein report a new photo-responsive supramolecular hydrogel based on a “caged” dehydropeptide (CNB-Phe-ΔPhe-OH <b>2</b>), containing a photo-cleavable carboxy-2-nitrobenzyl (CNB) group. We have characterized this hydrogel using a range of techniques. Irradiation with UV light cleaves the pendant aromatic capping group, to liberate the corresponding uncaged model dehydropeptide (H-Phe-ΔPhe-OH <b>3</b>), a process which was investigated by <sup>1</sup>H NMR and HPLC studies. Crucially, this cleavage of the capping group is accompanied by dissolution of the hydrogel (studied visually and by fluorescence spectroscopy), as the delicate balance of intramolecular interactions within the hydrogel structure is disrupted. Hydrogels which can be disassembled non-invasively with temporal and spatial control have great potential for specialized on-demand drug release systems, wound dressing materials and various topical treatments. Both <b>2</b> and <b>3</b> were found to be non-cytotoxic to the human keratinocyte cell line, HaCaT. The UV-responsive hydrogel system reported here is complementary to previously reported related UV-responsive systems, which are generally composed of peptides formed from canonical amino acids, which are susceptible to enzymatic proteolysis in vivo. This system is based on a dehydrodipeptide structure which is known to confer proteolytic resistance. We have investigated the ability of the photo-activated system to accelerate the release of the antibiotic, ciprofloxacin, as well as some other small model drug compounds. We have also conducted some initial studies towards skin-related applications. Moreover, this model system could potentially be adapted for on-demand “self-delivery”, through the uncaging of known biologically active dehydrodipeptides.
publishDate 2021
dc.date.none.fl_str_mv 2021-03-11
2021-03-11T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/1822/72634
url http://hdl.handle.net/1822/72634
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Jervis, P.J.; Hilliou, L.; Pereira, R.B.; Pereira, D.M.; Martins, J.A.; Ferreira, P.M.T. Evaluation of a Model Photo-Caged Dehydropeptide as a Stimuli-Responsive Supramolecular Hydrogel. Nanomaterials 2021, 11, 704. https://doi.org/10.3390/nano11030704
2079-4991
10.3390/nano11030704
https://www.mdpi.com/2079-4991/11/3/704
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute (MDPI)
publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute (MDPI)
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
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repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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